2-(Methylsulfonyl)ethanamine → 2,6-Difluoro-N-{3-[5-(2-{[2-(methylsulfonyl)ethyl]amino}-4-pyrimidinyl)-2-(1-pyrrolidinyl)-1,3-thiazol-4-yl]phenyl}benzenesulfonamide

HRID 590098Notes

Reaction equation

HRID 590098 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([CH3:7])(=[O:6])=[O:5].Cl[C:9]1[N:14]=[C:13]([C:15]2[S:19][C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[N:17][C:16]=2[C:25]2[CH:26]=[C:27]([NH:31][S:32]([C:35]3[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=3[F:42])(=[O:34])=[O:33])[CH:28]=[CH:29][CH:30]=2)[CH:12]=[CH:11][N:10]=1>>[F:42][C:36]1[CH:37]=[CH:38][CH:39]=[C:40]([F:41])[C:35]=1[S:32]([NH:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([C:16]2[N:17]=[C:18]([N:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)[S:19][C:15]=2[C:13]2[CH:12]=[CH:11][N:10]=[C:9]([NH:1][CH2:2][CH2:3][S:4]([CH3:7])(=[O:6])=[O:5])[N:14]=2)[CH:26]=1)(=[O:34])=[O:33]

Participants

3

Reactant 2

HCID 43405612-(Methylsulfonyl)ethanamineHCID 57989807N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1-pyrrolidinyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamide

Product 1

HCID 579896542,6-Difluoro-N-{3-[5-(2-{[2-(methylsulfonyl)ethyl]amino}-4-pyrimidinyl)-2-(1-pyrrolidinyl)-1,3-thiazol-4-yl]phenyl}benzenesulfonamide

Procedure

Following a procedure analogous to the procedure described in Example 1 using 2-aminoethyl-methyl-sulfone (923 mg, 7.49 mmol) and N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1-pyrrolidinyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamide (400 mg, 0.749 mmol) the title compound was obtained as a white solid (27 mg, 4% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.87-11.12 (m, 1H) 7.75 (d, J=5.4 Hz, 1H) 7.55-7.72 (m, 1H) 7.24-7.38 (m, 1H) 7.10-7.25 (m, 4H) 7.08 (d, J=7.8 Hz, 1H) 5.57-5.85 (m, 1H) 3.54-3.70 (m, 2H) 3.29-3.43 (m, 7H) 2.88-3.05 (m, 4H) 1.86-2.04 (m, 3H). MS (ESI): 621.1 [M+H]+.

Sources & evidence

ORD record
ord-139576bcf3344b518027eff0cea25301
Source dataset
uspto-grants-2016_01
Patent number
US09233956B2

Reaction notes

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